The Story of Brian ‘Sailor’ Roberts – One of the most famous poker legends of the 20th century

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The Early Years of the Gambler

Imagine a small town in Texas in the early ’30s, just in the middle of the white heat of the Great Depression. This low-rise, densely populated town is poor and a little dirty, with nothing but bleak prospects on the dust-swept horizon. Such towns in Texas often have Spanish names, right? Well, that particular one is San Angelo. And this is the place where Brian ‘Sailor’ Roberts, one of the world’s most famous poker players in the world, was born on March 7, 1931.

The Great Depression was coming to an end when his childhood ended too; as at the age of 12, he had already managed to get a golf caddy job. This helped his family to make ends meet. It also helped Brian develop a penchant for gambling: the favorite pastime of caddy boys was shooting craps. The idea of getting lucky and hitting the big time – “just to get the hell outta here, you know!” – must have been planted in Brian’s head as early as back then. Because in those days, many young boys were looking for a way out.

We do not know much about Brian’s early years, nor how successful he was in his studies. But he was one of the best football players at his school. And when the time finally came to make up his mind about whether or not to attend college, he decided to join the Navy. At this point in time, the Korean war was going full tilt, but the navy had not been involved in the war all that much yet; so the young sailors used to enjoy spending their time shooting craps and playing cards. And before long, Brian Roberts got pretty good at gambling. He managed to win some money, and they began to call him a nickname: ‘Sailor.’

Having come back to his dust-covered hometown in Texas, ‘Sailor’ Roberts quickly figured out that San Angelo didn’t really have anything to offer him. He had already traveled the world as a sailor; while also taking the chance to test the waters with some exciting gambling adventures too! And even though he was looking for some serious gambling income, San Angelo was definitely not the place to find it! So Brian Roberts finally hit the road.

Becoming the Road Gambler

Roberts had been hopscotching small towns, playing low stakes poker games and crushing the tables here and there. It seems he was constantly practicing to improve his skills. His bankroll must have been getting more sizeable, too; and he was seen to be playing high-stakes games more and more over time.

As Brian Roberts had already been traveling around for years, it was pretty logical that sometimes he would have to say hello to the same people he had already met by the poker tables. He made friends with Doyle Brunson and Amarillo Slim. Once, when three of them were playing, Thomas managed to clean out Brian and Doyle completely, but generously decided to give his opponents a partial cashback for their next games.

The roads were never safe in those days, especially for any gamblers carrying their winnings on them. Highway robbery was a serious threat; so Roberts, Preston, and Brunson decided to team up and began traveling together, sharing their gas and motel expenses. Soon they found it convenient to pool their bankrolls and to share their wins and losses. Doyle is said to have been a much better bankroll manager. And as his friends really appreciated that, they used to give him half of the total winnings of the team.

And on top of their poker escapades, they also played a lot of bridge, having beaten the most famous bridge players. The trio also tried to bet on sports, and they were pretty successful with that as well. So all in all, a truly formidable road team!

Claim to Fame

This trio of Texas road warriors had been crisscrossing the state for six years, slowly but surely becoming legends and cherishing a hope that one day they would come to Las Vegas and get their chance to crush some high-stakes tables out there. And that was exactly what they attempted in the late 50s! We don’t really know whether they were just that little bit too confident and underestimated their tough Vegas opponents, or just suffered from a massive losing streak – many gamblers know that both good luck bad luck often come in streaks – but however that may be, they actually did fail to really take Vegas by storm! So the trio lost all their money.

Roberts, Preston, and Brunson decided to part ways in gambling; but still choosing to remain friends. And they really did remain true friends! So much so, that in the early 60s, Brunson was hospitalized with a tumor in his throat, and Roberts immediately abandoned everything he was doing at that moment and came to support his friend, eventually staying with him for a whole two weeks. Fortunately, Brunson was lucky enough to recover, and the friends decided to reunite and continue their adventures.

In 1961, the Federal Wire Act was adopted. It banned phone calls for sports betting and bookmaking across state lines. Preston and Brunson quit sports betting, but Roberts did not – and ended up with a jail sentence for illicit bookmaking! One year in prison was enough for him to decide to never again attempt trying his luck in sports betting unless it was legal, like in Vegas.

Poker games did not have a strong foothold in Vegas in the early 60s, as these were played mainly in small downtown venues. High rollers were not seen there so often, and the overall gambling status of poker was much lower than nowadays. The man to change this, however, was Benny Binion – another legendary character of gambling history!

Despite positioning himself as a Texas cowboy with exactly the kind of authentic persona and  lifestyle we’ve come to expect, he was the one person who really succeeded in swapping the sawdust for the luxury carpets of the casino and boosting the prestige of the game: so he ended up dispatching plush limousines for customers traveling to and from the casino, along with some free drinks and some other coms (complimentary items). The Binion’s Horseshoe contributed to the growing popularity and fame of poker games. Roberts, Preston, and Brunson – the Texas Road Gamblers – were frequent guests.

Benny Binion used to arrange heads-up matches of poker high-rollers, cherishing a very special dream of his: he wanted to launch a tournament for the professional poker players out there! And so it was that in 1970, the first WSOP tournament was held in Vegas. There were only seven contestants, each of which had been individually invited by Benny Binion. They were all true poker legends of the era: Johnny Moss, Crandell Addington, Carl Cannon, Puggy Pearson, and the trio Texas Road Gamblers. The role Sailor, Doyle and Amarillo Slim had all played a key role in contributing to the overall success of the WSOP overall success; and it is impossible to overestimate the part they played in taking poker games to their current level of appreciation and popularity.

In 1974, Brian ‘Sailor’ Roberts won his first WSOP bracelet ($5,000 Deuce to Seven Draw event)! Then another WSOP bracelet followed in 1975.

What Kind of a Man Was ‘Sailor?’

The poker career of ‘Sailor’ didn’t develop in a stable manner over time. His net worth grew and collapsed many times as he went on. Even so, his friends used to lend him money when he was getting completely broke. But it seemed like the money was of no real value to him. He valued the game of poker itself, its exciting atmosphere and of course the friendship element – but perhaps he was just too enthusiastic, often playing in a way that was a little too hasty and risky for comfort.

He is also said to have been unreasonable with money – borrowing just to loan money to some other gamblers who were never going to give him the money back anyway. One possible explanation of this comes from Doyle Brunson, Sailor’s best friend, who said that Brian was a very kind and generous person, and had a heart of gold. Perhaps some people just exploited Brian’s kindness!

But he surely must have had a certain disdain for money – just like many other prominent poker players. According to Amarillo Slim, Sailor generally didn’t care to pick up a black hundred chip he had dropped and would choose to throw another one in the pot instead!

By the early 90s, he was already playing differently – tight and slow, and even quitting early. Drugs had already irreversibly damaged his mental and physical health by that time. He looked and felt really unwell. But he is said not to have had any problems with drugs until late in his life. There are allegations that as women were his weakness, there must have been a woman behind this late drug abuse story? However, by this point, it seems unlikely we’re ever going to find out the real truth.

On June 23, 1995, at the age of 6, Brian ‘Sailor’ Roberts died from cirrhosis in the Los Angeles hospital. Doyle’s wife Louise was there to hold his hand.

In 2012, he was inducted into the Poker Hall of Fame.

Roberts, Preston, and Brunson belonged to a real galaxy of men who both spiritually and mentally were the part of the Old West legacy – with life-long friendship, loyalty, and honesty being their core values. Keeping their word in a verbal wager was a point of honor to them: a truly sacred commitment! And perhaps that, in the end, is an even more important legacy of theirs than their remarkable success in the world of professional poker.

The Most Popular Questions About Poker

If any of you want to finally start your exciting poker career, we have prepared a section here to help you find the answers to the most popular questions. Get the answers to your questions straight away!

• What does poker A mean?

This rule in poker means the player can’t reach into his pocket for money during the hand. You can only contribute the exact amount you have in front of you. So if you run out of chips, a side pot will be created in which you won’t have any interest.

• How can you play poker for free?

You can download some free secure software and play poker for free. However, you won’t be able to enjoy the thrill of withdrawing your winnings. So this is why most players prefer online poker for real money.

• What is the best online poker?

There are many good websites that are ready to offer you access to the game. Choose a trustworthy casino with reliable licenses, then go on to play and enjoy your winnings! You can also choose some famous online poker providers to help start your high roller career.